Agent Scott Boras spoke to the media at the Winter Meetings yesterday and was asked if the Orioles had reached out about extension talks with his clients Gunnar Henderson and Jackson Holliday. “Only once or twice a day,” Boras quipped, with Andy Kostka of The Baltimore Banner among those who passed his comments along. “Those kinds of things, obviously we listen, and Mike [Elias] and I talk a lot. Obviously, our job is to filter those phone calls and relay them to the player, and kind of discuss it and see if it’s something that the player himself is interested in.”
Boras and his clients have a reputation of generally being averse to extensions, though that’s not to say they never happen. MLBTR’s Contract Tracker shows that Boras has negotiated extensions for clients such as Xander Bogaerts, Stephen Strasburg, Lance McCullers Jr. and more.
Both Henderson and Holliday are fairly inexperienced but extensions for players at this stage of their careers are becoming more common. Henderson has 184 games under his belt, but has thrived in those, winning American League Rookie of the Year here in 2023. Holliday has yet to make his major league debut but is the consensus top prospect in the sport.
In recent years, players like Luis Robert Jr. and Eloy Jiménez have received notable extensions prior to even making it to the big leagues. Jackson Chourio, who currently falls just behind Holliday on those prospect lists, recently set a new benchmark for players with zero service time. He and the Brewers agreed to an eight-year, $82MM extension with performance bonuses and a pair of club options. There have also been notable deals given to players with a small amount of major league experience, with each of Corbin Carroll, Wander Franco and Julio Rodríguez getting nine-figure guarantees.
For the Orioles, they would have to change strategy to get a deal done with either player. Since Mike Elias was hired as general manager in November of 2018, the largest guarantee they have given to anyone is the one-year, $13MM deal they gave to Craig Kimbrel this week. The only extensions they have signed were two-year deals for John Means and Félix Bautista. In both cases, the player was rehabbing Tommy John surgery and was already under club control for the two seasons covered by the contract.
To be fair, the O’s have been aggressively rebuilding for much of the Elias tenure, so big spending wasn’t warranted. But they won 83 games in 2022 and still kept this modest last winter. The current offseason is still ramping up, so maybe there’s a bold move or two to come, but there’s been nothing too out-of-character just yet.
Due to that lack of spending, the club has the financial means to theoretically do anything it wants. The only commitments on the books for 2025 are $1MM owed to Bautista and another $1MM for the buyout on Kimbrel’s option. There’s nothing committed for 2026. Per the data of Cot’s Baseball Contracts, the O’s had a payroll as high as $164MM in 2017, which put them in the top 10 league-wide. But much has changed since then.
Owner Peter Angelos collapsed in 2017 due to the failure of his aortic valve and his son John Angelos later was named “control person” for the club. Since then, the club has been rebuilding and keeping player costs to a minimum. Beyond that, they haven’t been able to agree to a new lease for their home ballpark, with the current agreement set to expire at the end of this month. It was reported earlier today that David Rubenstein is attempting to purchase the club, though it’s unclear if he has a chance of succeeding or how long that would take.
There’s plenty of long-term uncertainty around the franchise so it’s an open question as to how much latitude Elias even has to commit future dollars to either of these players or any of the other on the roster. The aggressive tanking of a few years ago helped them load up their farm system, which has led to their current club being filled with talented youngsters like Adley Rutschman, Kyle Bradish, Grayson Rodriguez, Jordan Westburg and more. Getting one or more of those players to put pen to paper and stay in Baltimore for a long time would be a sensible strategy, but the likelihood of such a deal actually happening isn’t obvious at the moment.
In the short term, Elias will have to think about putting the best possible team on the field for 2024 and recently spoke to Rich Dubroff of Baltimore Baseball about that. They are set to have an outfield of Cedric Mullins, Austin Hays and Anthony Santander, though there are some different options for a fourth outfielder, with Elias naming Heston Kjerstad, Colton Cowser, Kyle Stowers and Ryan McKenna as suitors for such a gig.
Kjerstad had a solid showing last year, tearing through Double-A and Triple-A before getting into 13 major league contests. The club probably wants to find him regular playing time somewhere, and he has played some first base before, but Elias shot down the notion of him moving there on a regular basis. “I don’t have designs on him becoming a full-time first baseman,” he said. “I think it’s something more that we’re trying to get it to a point where it’s in his back pocket and we can tap into it a couple of days a week.” The club has Ryan Mountcastle and Ryan O’Hearn as options for first base and designated hitter, so it’s not even a guarantee that there’s a cleaner path to playing time for Kjerstad there.
Despite all the crowding, the O’s have some openness to bringing in another outfielder, though it seems the odds of that happening are low. “I still see a ton of playing time and a lot of at-bats outside of our three primary outfielders,” Elias said. “Right now, this is up for grabs. These guys, I don’t think any of them have really proven it yet over a long period of time in the majors, so we’re cognizant of that. If we can find external insurance or external help in this department, it’s not going to close the doors for those guys, and it wouldn’t be unwelcome from our end, either. Competition is good. Depth is good. These seasons are so unpredictable. Odds are you’ll get some injuries, so we have to prepare for all that. We’ll talk to free agents that might be a fit for joining our outfield mix, but we have high hopes for the names that I mentioned.”
Nothing grows the value of a franchise for sale like young stars under long term team control. No matter who owns this franchise, they are going to want to keep those two guys in Baltimore their entire career.
Who wins an MVP award first, Holliday or Rutschman?
Who Knows?
Plus Rutschman isn’t perfect
You can have O’Hoppe, Adell, Canning, and Rendon for Rustschman.
I am not trading him, but I think Wieters was just as good as Rutschman.
Rutschman has one major flaw, he can’t throw straight sometimes
Rutschman put up as much value in his 1st and 2nd seasons as Wieters did in his 3rd and 4th. Plus Rutschman is a much better hitter. There’s a good comparison there, but I think Rutschman is better.
Rutschman is also a much bigger clubhouse presence and better game caller.
“You can have O’hoppe”…Is that a threat or a promise?
Wieters had no team his first few years
Going out on a limb here, but guessing Baltimore declines that.
I’m going to go with Adley but the future in Baltimore is so freaking bright. These two and Gunnar may be on MVP ballots every year for the next decade.
Gunnar.
I think Henderson wins an MVP before Rutschman or Holliday. I hope the O’s extend all three, but Gunnar should be first in line.
I have a bias towards catchers. They provide so much more value than the popular numbers show. Calling a good game behind the plate alone is so valuable.
But the voters rarely consider catchers due to the lack of slash line and HR so probably Holliday.
Rutschman has that intangible quality that is hard to describe but easy to define. He’s a winner. Extend him first.
Not addressing the pitching is going to cost them again…another early playoff exit in the Cards if they don’t do something. Don’t cheap out.
Pitching was better than the Rangers, they just pitched poorly on the playoffs.
@Arnoldpsufan you have no clue. In what world is Kyle Bradish, Dean Kremer, and Grayson Rodriguez better than Nate Eovaldi, Jordan Montgomery, and Max Scherzer? Kyle Bradish is a third starter on 90% of teams while Kremer and Rodriguez are 5th starters. Eovaldi is an ace, Scherzer is a 2 or a 3 at his age, and Montgomery is a solid 3rd starter. These guys have experience in the playoffs and consistent success. Orioles lack relief as well. They have a lot to improve on, thats for sure. The GM Elias did absolutly nothing at the deadline last year even though he had all the prospects to make a big splash
“you have no clue” then proceeds to call Kyle Bradish a #3 despite finishing 7th in cy young and Grayson Rodriguez a 5th starter lol.
Lots of average pitchers have finished 7th in cy young.
Starters of his equivalent come and go.
The trio of Ms,Ne,Jm are far and away the superior choice and it’s not even close.
If bradish can repeat his success for another 3 seasons, the Orioles are halfway there
Calling Nathan Eovaldi an ace is the biggest laugh for me.
@BrianStrowman9 who was the Ace of the 2018 Redsox and the 2023 Rangers then? You know, the teams that both won a world series
Eovaldi is an ace when he pitches, but he’s been a part-timer for most of his career because of injury. He’s had two TJ surgeries, and he missed significant time this year with “forearm tightness.” The Rangers were obviously cautious because of his injury history by only offering a two year deal with a vesting 3rd year after 300 innings pitched. Any team would want him on their staff, but he’s a high risk, high reward pitcher at this point in his career.
There’s really no excuse not to try and lock up at least a few of their current young stars and/or soon-t0-be stars. Look at how much some of these older free agents now cost. Imagine if you had someone like Soto on a 8-year $82m deal like Chourio just got.
Sure, some of these contracts will turn into duds at some point, but I THINK billionaire owners can afford to have a bad contract now and then.
Exactly. Even if Chourio is only league average instead of a perennial all star, ~$10M AAV is absolutely nothing to a billionaire. Extending these guys is good for the player, good for the team, good for the fans.
“$10M AAV is absolutely nothing to a billionaire”…Go ask any billion aire to loan or give you $10M and you will find they don’t consider it “nothing”…I think if you looked into the facts, you would find that billionaires are some of the cheapest people around and didn’t get to be billionaires by wasting or throwing away money.
Giving that money to me would be throwing it away. It’s not wasting money to extend past arb years at a low AAV if that player is a potential superstar. For Chourio and these Baltimore youth it’s a good bet. Evan White and Senzel getting deals when they never had that upside is a different story.
Henderson is the total package. I’d look at a deal that grants him free agency at 29 or 30 so he can look for a mega deal
Boras, always talking himself up, trying to be more important than the game itself. Wait a bit on those long time commitments on freshman players. See what their sophomore years bring as the League forces them to change their approach.
Boras is a salesman. That’s what his clients expect from him.
I’ll never understand why people get mad at Scott Boras. That guy has made more money for his clients than any other agent in the game’s history. He’s great at what he does. You look at Acuna’s contract (8/$100) while a lot of money is not nearly what he would have gotten on the open market had he waited through arbitration. Boras would have never allowed him to sign that contract. If I were a ballplayer I’d want him to be my agent.
Right !!! Acuna and Chourio – 2 worst deals in mlb history ! Boras would renounce his position in dealings before letting one of those 2 sign those ridiculous deals !
Acuna is playing great on his current contract. Chourio is debatable but lots of teams do this.
They’re bad for the players is what he’s saying, not for the teams.
Once Rutschman gets going, he’ll be reminiscent of Gary The Kid Carter. He has good pop, a good glove, good presence and always seems to be in a good mood.
Extensions are all the rage nowadays. No one wants to bet on themselves to be Mega Global stars Oh wait, MLB doesn’t have any global stars.
“Doesn’t have any global stars”..There’s this one guy named Ohtani, you may have heard of him, but apparently you don’t watch much baseball.
@mlb fan
Never heard of him.
I hear Josh and Bo Naylor’s dad is pretty good with computers….you might want to get some protection…
Going to be interesting to see how this trend of extending guys before debuts goes. On one hand, getting a superstar for less than 20 a year is a crazy bargain, but one of these guys is gonna flop at some point. High risk, high reward for sure
Jon Singleton happened a long time ago and the extensions have only grown since then.
It is a calculated gamble on both ends. Teams know sometimes they will lose.
Getting the son of a wealthy former major leaguer, who already has a huge signing bonus, to sign away the full earnings potential of his 20s won’t be easy, especially with Boras as his agent.
Let’s be real, knowing the floors/ceilings of their career lengths and values, the starting points on extensions would be something like::
Gunnar Henderson: 18 years/$585M ($5M signing bonus, $1M, $2M, $12M, $20M, $30M, $35M, $37.5M, $37.5M, $37.5M, $37.5M, $40M, $40M, $40M, $40M, $40M, $42.5M, $42.5M, $45M)
Jackson Holliday: 20 years/$705M ($10M signing bonus, $2.5M, $5M, $12.5M, $20M, $30M, $35M, $35M, $37.5M, $37.5M, $37.5M, $37.5M, $42.5M, $42.5M, $45M, $45M, $45M, $45M, $45M, $45M, $50M)
That’s just the reality with the way salaries are. These are not guys who are going to give the team discounts. Nor should they be.
I hope this is a joke. Holliday is definitely a better prospect than Chourio, but if he got 8/82 then what could possibly make you think Holliday would get THAT much?
And even if he somehow could, why would the Orioles do that? Those AAVs are basically what he would top out at if he signed a deal in his prime, so why take the risk now when you wouldn’t even be saving anything down the line? I agree that salaries are only going up but this is pretty extreme lol
Ask Boras if he’s joking
They will get that on the open market one day if they hit their ceiling or near enough
I don’t doubt that down the line with salary inflation that they can come close to those numbers if they reach their potential (after all, we’re talking 10-20 years down the line here).
But I think that’s the max end of it and that’s if everything goes perfectly, so if you’re the Orioles why would you take that risk now if you’re not saving anything? At that point it would be smarter to take it year to year and lock them up closer to free agency.
Right. I am saying with Boras as their agent, that’s what it would take to get him to listen, because at the point at which they’d hit arbitration and free agency, those would be relatively typical salaries and not even top top of market, so they’d be discounting themselves by $1-5M a year anyway and like $20M to $100M overall.
Here’s the thing, lets say you extend them both for 8 years- even at a robust $25M for just the final two years of those deals, Boras would consider it too much of a lowball and giving up too much of their prime.
That same deal being discussed for them with Boras as their rep and with them being seen as the futures of their team, future stars of the league, already well on their way establishing themselves as formidable and legitimate stars, would, pure and simple, have to start at 8 years/$164M or something and even then, Boras would tell them it’s too low ball a deal and they shouldn’t take it, despite how much money it would be to a normal person or to a less name brand but high profile prospect. He’d tell them “for some other guys? That’s the best deal they can get and they should take it, but for you as my client and you as the player you are, etc. you are leaving tens of millions on the table in those eight years and you are potentially leaving tens of millions on the table from a future deal, depending on how this deal would work out. Don’t be Ronald Acuna, Jr.”
They will almost be able to afford bacon on their burgers for the rest of their lives..
Get it done!
Ya think?
I’d love to see the Orioles lock them up. I love it when teams have a competitive window with a core that stays together for years.
I have no respect for owners who tank on purpose and get all the top prospects…
The Astros have latest successful rebuild. It’s risky but its business at the end of the day.
“…openness to bringing in another outfielder”. Heck, just bring back Aaron Hicks.
A deal for Henderson probably looks similar to Wander Franco’s deal = 10 or 11 years at around 20m per. His curve will probably be C > 1B > DH, and if he wants stability and security then that might work.
Holliday is tougher because he is younger with a higher ceiling. I think the Os would need to surpass what Chourio got to even be considered, maybe 10/145. That would let him pick up maybe another 3 or 4 year deal depending.
There’s zero chance Angelos signs off on either of these, though.
I don’t think Boras or Holliday’s father would let him sign an early extension offer.
And I don’t think Boras would let Henderson do it, either.
I think between Matt Holliday and Scott Boras, they’re going to get talked into either signing early for market value or going year to year and signing for a free agent market value extension with their original club, that matches and possibly slightly exceeds their market value.
Holliday would hit FA at 29. He could realistically get a 6-7 year deal at that age if he’s anywhere close to his ceiling.